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Oswego holiday lettings

We found 160 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Oswego that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Oswego

Showing deals for:30 Jan - 6 Feb

Image gallery for Beautiful Peaceful 3 Bedroom Home in Plainfield

Living area
8.6 out of 10, Excellent, (7 reviews)
Excellent
(7 reviews)

Beautiful Peaceful 3 Bedroom Home in Plainfield

Plainfield, IL

8% off
Price is £2,497
for 7 nights, 1 home
£357 per night
includes taxes & fees
Beautiful Peaceful 3 Bedroom Home in Plainfield

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Travel to arty Oswego

The area's art galleries and museums are just some of the reasons to come on holiday to Oswego. Travellers to this romantic city praise the restaurants, shopping and bird watching. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Oswego

Are you searching for top things to see and do in the area? Venture out of your holiday home and check out everything that makes Oswego a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Fox Valley Winery (0.8 mi / 1.4 km)
  • Bolingbrook Golf Club (10.5 mi / 17 km)
  • Mistwood Golf Club (12.3 mi / 19.9 km)
  • Cantigny Golf Club (15.2 mi / 24.5 km)
  • Seven Bridges Golf Club (15.6 mi / 25.1 km)
  • Grundy County Speedway (19.1 mi / 30.8 km)

Exploring the natural features in Oswego

Whether you're an outdoor enthusiast or just want to take in the scenery, Oswego is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Centennial Beach (11.7 mi / 18.9 km)
  • Riverwalk Park (11.8 mi / 18.9 km)
  • Fabyan Villa Museum & Japanese Garden (13 mi / 20.9 km)
  • Blackwell Forest Preserve (14.2 mi / 22.8 km)
  • Morton Arboretum (18.1 mi / 29.2 km)
  • Forest Preserve District of Will County (21.1 mi / 33.9 km)

Transport options to and around Oswego

Fly into Chicago, IL (DPA-Dupage), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago O'Hare International Airport (ORD), which is 30.7 mi (49.4 km) away.

Frequently asked questions

What is the best area to stay in Oswego when booking a holiday rental?
When considering a holiday rental in Oswego, Illinois, a popular area to stay in is the charming downtown district. This vibrant neighbourhood offers a delightful mix of local shops, cafes, and restaurants, superb for immersing yourself in the community's atmosphere. Staying here places you within walking distance of the scenic Fox River, which is ideal for leisurely strolls or bike rides along the riverfront trail.

Another appealing option is the area around the Waubonsie Lake, which provides a peaceful retreat with stunning views and opportunities for outdoor activities such as fishing and picnicking. This location is particularly attractive for families, as it offers playgrounds and open spaces for children to enjoy. Plus, the lake is a short drive from the popular Hudson Crossing Park, where you can explore walking paths and enjoy seasonal events.
How much does it cost to rent a holiday home in Oswego?
Prices for holiday rentals in Oswego vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oswego to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oswego holiday house rentals?
You can find great discounts on house rentals in Oswego on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Oswego?
In Oswego, apartments, holiday houses, and condos are all popular types of holiday rentals, with several options available in the area. These rentals are typically found in quiet neighbourhoods that offer a suburban atmosphere, great for families or travellers seeking a peaceful stay. Most apartments come equipped with modern amenities such as fully equipped kitchens, comfortable living areas, and often access to communal facilities like pools or fitness centres.
Are there any family house rentals in Oswego?
In Oswego, Illinois, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhoods here offer spacious homes equipped with amenities like multiple bedrooms, full kitchens for preparing meals, and comfortable living areas for family gatherings. Many properties also feature outdoor spaces, superb for kids to play or for family barbecues.
Can I find long-stay holiday rentals in Oswego?
A long-stay holiday rental in Oswego is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oswego?
In Oswego, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these rentals offer spacious layouts and amenities such as fully equipped kitchens and private outdoor spaces, great for enjoying time with pets.
Are there any remote work holiday rentals in Oswego?
In Oswego, Illinois, there are several remote work holiday rentals available to accommodate travellers looking for a productive environment. Many of these properties come equipped with essential amenities such as dedicated office spaces, desks, ergonomic chairs, and reliable Wi-Fi, making them suitable for both work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oswego holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oswego with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oswego?
In Oswego, popular holiday rental amenities include well-equipped kitchens featuring essential appliances like refrigerators, microwaves, and cookware. Many properties also provide coffee makers, allowing guests to enjoy freshly brewed coffee at their convenience. These amenities cater to travellers seeking a cozy feel, ideal for preparing meals and relaxing after exploring the charming local area.
When is the best time to visit Oswego for a holiday rental?
July is the most popular time to visit Oswego, Illinois, drawing travellers to enjoy the warm summer weather and vibrant local activities. From May to July, the peak season offers an array of outdoor adventures, including kayaking on the Fox River and exploring the picturesque parks that dot the area. Visitors can also engage in local festivals, farmers' markets, and community events that showcase the charm of this delightful town.

During July, temperatures typically hover in the mid-20s Celsius, providing great conditions for sightseeing and outdoor fun. The long days and pleasant evenings create an ideal atmosphere for barbecues, picnics, and enjoying the local dining scene.

If you're looking for a more budget-friendly option, consider visiting in November. While this month falls outside the peak tourist season, it offers a great experience with the onset of autumn, providing a quieter atmosphere to explore the area's scenic beauty. Plus, you'll have the opportunity to witness the lovely transition of the landscape as the leaves change colour.
How early should I book a Oswego holiday rental?
Book your Oswego holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Oswego home rental booking on Vrbo?
To find Oswego holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oswego holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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